Style Shrink

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Wearing a stylish (dress) shirt untucked over shorts is difficult where these shirts are generally too long (and meant to be tucked in). Any suggestions for a shorter smart casual shirt (no Tee or polo of course) that looks great on shorts when untucked? To be matched with Santoni or Tod's loafers of course.

Dear Style Shrink...

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One of the things that I (and my girlfriend, for that matter) pride myself on is dressing well whatever the occasion. I am not a huge fan of summer as it’s often too hot for me and this reduces my choice of clothing. I particularly struggle with pairing footwear and socks with smart chino-style shorts. I usually prefer to wear a collar, mainly shirts but polos occasionally, too, and therefore don’t want anything too casual on my feet.

Dear Style Shrink...

Dear Style Shrink...

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I want to buy a second-hand TAG Heuer Monaco as worn by Steve McQueen with a blue dial and black strap. However, I only ever really wear brown shoes. Should the strap match my shoes, my belt or both? Secondly, can you recommend a reputable shop or website that might sell a pre-owned Monaco?

Dear Style Shrink...

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When does a shoe become too pointy? I picked up a pair of Church’s loafers a couple of years ago. I have hardly worn them because I read everywhere about how men hate pointed shoes but nobody seems able to tell me what is too much.

Dear Style Shrink...

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I have trouble finding suitable neckwear for a blue-black peaked-lapel jacquard wool suit. The thing is, it’s not really a formal suit and I don’t know which tie fabric to choose or how wide it should be. Can you just choose any tie that would go with a regular notch lapel suit, or would a bow tie be more appropriate?